


I Knew You Were Waiting For Me

by bryzknowstheuniverse



Category: IT (2017), IT - Stephen King
Genre: Anal Fingering, Anal Sex, Background Mike Making All The Panties Drop, Background Stenbrough, Blow Jobs, Cute Fluffy and Smutty, First Kiss, First Time, Friends to Lovers, M/M, Reddie, background benverly
Language: English
Status: Completed
Published: 2017-12-11
Updated: 2017-12-11
Packaged: 2019-02-13 10:33:18
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 3,218
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/12982185
Author URL: https://archiveofourown.org/users/bryzknowstheuniverse/pseuds/bryzknowstheuniverse
Summary: A very inexperienced Trashmouth losing his v-card to a far more experienced Eddie Spaghetti.





	I Knew You Were Waiting For Me

**Author's Note:**

> Requested by a lovely anon on my Tumblr, thegreatwhiteferret.

Richie Tozier has a big mouth and a wild imagination. He’s been bragging about his sexual conquests to the other Losers since middle school. Underneath all the bravado lies the truth; Richie is seventeen and he’s a virgin. For the longest time he held out hope that he wasn’t the only one, but his hopes were dashed one by one. 

 

Mike was first. Big, strapping, and handsome. He was amazing at football and even with the racial tension in Derry, he made all of the girls’ panties drop. When he made varsity as a freshman, the head cheerleader, Heather Sinclair, took it upon herself to welcome him to the team...and his sexual awakening. Mike had told them all about it, flush faced and jittery, and Richie had chirped him saying that it was about damn time he join the club. A string of girls followed after Heather, but Mike was still his genuine heart of gold self. Richie secretly wondered if he thanked the girls for spreading their legs for him as he walked them home.

 

Ben and Beverly were next. They were a bit more cliche than anyone had expected. Roses and a hotel room on Valentine’s Day, their sophomore year, but Bev secretly loved it. She had gushed to Richie about it during one of their smoke breaks, and Richie had pretended to gag. Ben was too much of a gentleman to share details, but the whole club knew that after their first time they were fucking like rabbits.

 

Stanley Uris went next, and took Big Bill with him. They had been flirting around the idea of being more than friends since Bill had broken up with Bev when they were freshman, but Bill was always too shy and nervous to act on it. He didn’t want to ruin his friendship with Stan. The other boy found this sweet, but was incredibly sick of it and pounced on Bill on the July 4th between sophomore and junior year. During the fireworks display he just leaned over and grabbed Bill, pressing his lips to his. They made out under the light display, but Stan needed more. He all but dragged Bill back to his house. Richie would find out later that Stan had given Bill a mind melting blow job before prepping his own asshole and riding Bill until they both came, making their own fireworks. Stan was more comfortable expressing himself out of that, wearing his pants a little tighter in the ass, and Bill was certainly more vocal about what he thought about his sexy ass boyfriend. Richie thought it was hilarious that they could be so buttoned up and reserved in their everyday lives, but complete freaks in the sheets. He got beep beeped when he voiced this to the group.

 

His last strand of hope and dignity died when Eddie went with his mom to visit his family out in Montana when they were sixteen. His cousin was having surgery and they needed an able bodied boy to help with the farm...Eddie was apparently the only one available. Eddie came back ripped and tan from all the manual labor, and with a damn good story about his first time. There had been a young ranch hand there, Jorge, with rippling muscles and a beard and he had taught Eddie all of his damn tricks. Eddie blabbered on about having his first blowjob while the sun was setting over the mountains, getting fingered while he knelt on rocks down by the quarry, and getting his pink hole licked open by a devilishly good tongue while his mom was in the next room. Finally, he told the story about how Jorge had fucked him so good in the barn that he cried. Richie blushed throughout these stories, trying to cover it up with sarcastic comments, but Richie was terrified. In his mind he had always thought that he and Eddie would end up together, that they would be each other’s first. 

 

Richie was scared to death now, scared to approach Eddie. What could he possibly have that would compare to that Jorge asshole. He was just an inexperienced virgin who had never even really had a first kiss. He stopped making his usual jokes after a while, he had lost his spark and had no idea how to get it back. 

 

It was two weeks before Halloween during his senior year. Richie was sitting in the library trying to study while his ADHD was working overtime. He had to focus on the calculus algorithms that his teacher had assigned in preparation for their big test, but he couldn’t. Eddie was sitting across from him, pink lips pouted as he read through his chapter on Reconstruction after the Civil War. The other Losers had bailed on the study session for a variety of reasons, but Richie hadn’t really pressed it. He and Eddie had hung out loads of times on their own. He was working through a particularly hard question when he noticed that Eddie was fidgeting a bit.

 

“Eds, my brain already has a hard time working right, please stop shaking.” Richie said, genuinely concerned about the task in front of him. Eddie apologized, but a few minutes later was back to his shaking. “Jesus, Eddie. What is going on in that brain of yours that you can’t sit still?” Eddie blushed.

 

“Hey, Rich?” Eddie started, nerves present in his voice. Richie dropped his pencil and gave Eddie his full attention.

 

“Yeah, Eds?” Richie could feel his stomach twisting, he didn’t like that Eddie was nervous to say something to him. They never had that problem. They were probably too honest by most standards.

 

“What...uh...what was your first time like? I know you’ve talked about a lot of different guys and girls, but I don’t know if I’ve ever heard the story of your first?” Richie went pale. He knew that he talked a big game, but he honestly figured that they all knew that he was lying. That it was all an act. He never would have expected that Eddie, his best friend, would believe his bullshit. He could continue the act, or he could just be honest with him. Cut the bullshit ask and just tell Eddie that he had made it all up because he was so shy about all of that stuff, and hadn’t done anything sexually.

 

“Honestly?” Richie asked, and Eddie nodded and looked at him expectantly. “I’ll...uh...I’ll have to get back to you on that one, Eds. I’m a virgin.” 

 

“Jesus. I don’t know why I was expecting a honest answer from you. God dammit. I just wanted to know the truth…” Eddie sighed, he was disappointed.

 

“No. Eds. I am telling you the truth. I’ve never done anything with anyone. Shit...I...I’ve never even really kissed anyone before.” Richie rubbed his temples, he could feel tears welling up in his eyes. Honesty hurt like a bitch.

 

“Oh.” Eddie squeaked out. Richie looked up to meet his eyes. “Richie. I’m sorry that I brought it up. I was just talking to the other Losers earlier and they mentioned that I should ask you. I...I didn’t know…”

 

“Nah. It’s okay. I just, it kind of scares me I guess. I’ve been talking it up for so long, and listening to you guys tell your stories and I’m just...I’m just worried that I’m going to be really bad at it.” Richie breathed out. Eddie frowned and moved around the table to sit next to his best friend.

 

“When you find someone who is worth your time, worth the brilliance that is Richie Tozier, you’ll be just fine. You’ll be better than fine, you’ll be amazing.” Eddie tried to reassure him.

 

“Ha. Sure.” Richie said, but there was no humor there. Instead a thought started to blossom in his mind. “Hey, Eds? Would you maybe...would you be my first?” Eddie’s face turned red, he had wanted Richie for a long time. Had thought that he wouldn’t be experienced enough for him, that’s why he had let himself fall for Jorge. Why he had the subsequently given into pleasure and let himself become someone new and adventurous. He wanted to ready for Richie, and be good for him. 

 

“Are you sure you want me to be that person?” Eddie asked, sort of ready for Richie to laugh in his face and tell him this was all a joke.

 

“Of course, Eddie.” Richie said, before a mischievous glint entered his eyes, “Besides it’s apparently much better with a friend.” Eddie punched him in the shoulder, but giggled nonetheless. He couldn’t deny that he loved Trashmouth and his humor. 

 

It was no secret that Eddie’s mom was way too overprotective. She had not gotten better even after Eddie called her out on her gazebo bullshit. There’s no way that she was going to let Richie into her house for even an afternoon study session, let alone to spend the night. If Eddie played super sweet for a full week, she might agree to let him sleepover at Ben’s house. She like Ben’s doting mother after all. So Eddie primed his mother all week, did extra chores, acted like a sweet little mama’s boy, and then asked on Friday afternoon if it was okay for him to stay at the Hanscom house on Saturday night. She agreed only after Eddie told her that he was going to be working on an important project for his English Lit class. 

 

Eddie of course had no plans to go over to Ben’s house. He had simply told Ben that he needed someone to cover for him, and Ben had agreed to be his lookout. He would intercept any calls if his mom decided that she needed to check on him. Eddie would be miles away, with Richie. He had the whole thing planned out. Mike was letting him borrow the farm’s truck, Beverly had gotten a whole bunch of fairy lights from her aunt’s flower shop, Bill and Stan had helped him find a whole bunch of pillows and blankets. All the Losers were in on it, well everyone except for Richie who was just told to show up to the orchard at the edge of the Hanlon farm on Saturday night at seven o’clock. 

 

Eddie looked at his handy work, well his, Ben, and Mike’s. Okay, mainly Mike’s. Ben and Eddie weren’t much of a help with the manual labor part of their plan. Mike had parked the truck between the rows of apple trees, he had then strung the fairy lights in the trees and hooked them up to a portable generator that they used on the farm. Eddie had set up the blankets and pillows in the bed of the truck. As it got darker, they turned the lights on and all three marvelled at the sight. It was beautiful. Everything was going to be perfect for Richie.

 

Bill and Stan had done their part by keeping Richie too busy all day for his nerves to build and cause him to self sabotage. Richie didn’t know that the rest of the club knew about his plans with Eddie, just figured that Bill and Stan were trying to get him to do their dirty work. It wasn’t unusual. Bev had shown up around five, Richie had asked if she would be able to drop him at the Hanlon farm. She had agreed, telling him that she needed to pick Ben up from Mike’s anyway. 

 

Richie walked along the Hanlon property line and into the orchard, he stopped in his tracks when he saw what Eddie had done for him. The lights twinkling in the trees, illuminating the bed of the farm truck, that was filled with pillows and cozy looking blankets. There was soft music flowing from the radio inside of the truck, and there was Eddie, beautiful as ever, waiting for him, standing right in front of him. Richie had tears in his eyes, no one had ever done something like this before, done something to make him feel special. 

 

“Eds, oh my God.” Richie breathed out, pulling the smaller boy into his arms. “This is amazing. I can’t believe you did all of this.”

 

“Of course, Rich. Anything for you. I wanted to make this special.” Eddie stood on his tiptoes and pressed a kiss to Richie’s lips, sweet and simple. It was his first real kiss after all. Eddie needed it to be special for him. It may have started sweet but it quickly began escalating. Eddie broke the kiss, pulling Richie over to the bed of the truck and climbing in, helping him to do the same. 

 

Eddie pushed Richie so that he was lying on his back and straddled his hips. He kissed him again, grinding his hips down into Richie’s slightly, pulling moans out of the other boy. Eddie sat up and peeled his shirt over his head, helping Richie to do the same. Their skin prickled a bit in the autumn air, but Richie knew that Eddie was about to warm him up. 

 

Eddie kissed down Richie’s neck, sucking a mark next to the hollow of his throat. He kept his kissing voyage going down Richie’s chest and stopped at the waistband of Richie’s Jeans. He unbuttoned the jeans and snaked his hand in, palming Richie’s growing erection. Richie threw his head back in pleasure, he wanted so much more.

 

“Lift your hips, baby.” Eddie whispered, Richie complied and Eddie pulled his jeans off with ease. He was left lying in front of Eddie in just his boxer briefs. “Mmmm, Richie, you look so good like this, strung out, are you gonna beg me, baby? Beg me to fuck you?” Richie whined, desperate for Eddie to touch him. “Or are you going to beg to fuck me. I’d be good with that too, anything you want.” Richie bucked up into Eddie’s touch at that thought. 

 

They shared another deep kiss, before Eddie was dropping his head to Richie’s crotch, pulling down the waistband of the boy’s underwear and letting his cock spring free. His cock was twitching under the attention of Eddie’s gaze. Eddie used his thumb to rub the slit, collecting drops of precum and sliding his hand down the shaft. He jerked lazily a few times, before moving his head down and licking just the slit, Richie groaned. Pleasure coursing through his body. Eddie took the head in, tongue working at his frenulum, then sunk his head down most of the way, using his hand to work what he couldn’t fit in his mouth. He slid his mouth up and down his cock, varying his speed as he watched Richie fall apart from just his mouth. Richie was getting close, Eddie could tell by the sounds that he was making, he pulled off and jerked him a few more times, edging him off of his orgasm slightly. Richie whined.

 

“Baby, are you going to finger me open or do you want to watch me do it myself?” Eddie asked, pulling a bottle of lubricant and a condom from underneath one of the pillows.

 

“C-can I w-watch you?” Richie asked, mind hazy with all of the feelings. He never imagined his first time being like this. Eddie nodded and stood up in the bed of the truck, pulling his pants and briefs down in one motion. He got on his knees, straddling Richie’s legs, ass towards Richie. He used one hand to brace himself, sticking his ass out further so that Richie would get a real show. He coated three fingers in lube and slid them down the crack of his own ass. He circled his hole with one finger, teasing, before he pushed his finger in. He moaned at the feeling, keeping still for a moment before wiggling it around and then began thrusting in and out. He made sure to moan and make little noises, so that Richie would know that he was enjoying stretching himself open so that Richie could slide in. Richie reached forward and held his ass cheeks apart, watching as Eddie’s fingers abused his own hole. He added another finger, twisting his wrist, loving the slight burn that came with the stretch. Soon enough he was able to pump three fingers in with little resistance. He turned around to face Richie who leaned up and met him for a kiss. “You’re so fucking perfect, Eddie Spaghetti.”

 

“Asshole! Don’t call me that when I’m about to let you stick your dick in me. Where are your manners?” Richie gave him a smirk and shrugged, but the smirk was wiped off of his face as Eddie tore the condom wrapper open and slid the latex down his shaft. Eddie poured a liberal amount of lube on Richie’s dick before shimming up his body on his knees and lining up the head of his cock with his hole. “Are you ready, baby?”

 

Richie nodded and Eddie lowered himself, slowly taking Richie in, inch by inch. He squeezed his eyes shut, focusing his breathing as he got used to the size. Richie stroked Eddie’s hip, his mouth falling open at the feeling of Eddie’s tight heat around him.

 

Eddie wiggled around gingerly, becoming more comfortable. He raised himself slightly before sinking down again. Richie cried out in pleasure, and Eddie was moaning. He kept grinding his hips, lifting them and slamming back down with more and more intensity. Both boys were withering messes. Richie knew that he wasn’t going to last very long, but he wanted to make it good for Eddie too. He wrapped his hand around Eddie’s dick, stroking experimentally. The smaller boy’s eyes nearly rolled back in his head. He slid up and down a few more times, Richie could feel the heat pooling already and couldn’t help himself, he tumbled over the edge and came with a shout.

 

Eddie pulled Richie’s hand off his cock and pumped furiously for another minute, cumming all over Richie’s chest. He moved off of Richie, before sliding the condom off and tying it, dropping in in a plastic bag. He used one of the blankets to wipe them off, and then tossed it to the side. Richie was waiting to pull him into his arms and pull blankets over them. Eddie smiled, resting his head against his chest.

 

“So, how was it, Richie?” Eddie asked snuggling in a bit more, the chilly temperature starting to get to him after being exposed to it for so long.

 

“Jesus fuck, Ed. So much better than I could have ever expected.” Richie rambled. “I love you. God I fucking love you. I want to do that with you so many more times. All the time. Jesus, I finally understand why the others are always sneaking off....” Eddie cuts him off by pressing a kiss to his lips.

 

“I love you too, Trashmouth. If I knew you were waiting for me, I would have waited a little longer too, just to have you as my first.” How about we get some sleep and see about a round two?” Richie’s eyes grew in size and he nodded eagerly. Eddie laughs a little, and they settle in. Counting stars until they fall asleep. 


End file.
